Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8975-8978

  Si Fodil, Mohamed ^a   Ferreira, Humberto ^a   Gralak, Jean ^a   Duhamel, Lucette ^a  

^a IRCOF   (France)

Author keywords

Enol ethers; Ketene acetals; Reduction; Retinoids

Indexed keywords

ACETAL DERIVATIVE; BROMINE DERIVATIVE; ETHER DERIVATIVE; KETENE DERIVATIVE; LITHIUM; LITHIUM DERIVATIVE; REAGENT; RETINAL; RETINOID; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

ARENE;

EID: 0032480961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02031-0     Document Type: Article

References (15)

1. [1] Hiouni A, Duhamel L, Tetrahedron Lett. 1996;37:5507-5510.
2. Compound 1 was also obtained by a similar procedure: Wei HX, Schlosser M, Tetrahedron Lett. 1996;37:2771-2772.
3. [2] a) Duhamel L, Duhamel P, Lecouvé JP, Tetrahedron. 1987;43:4349.
4. b) Duhamel L, Ancel JE, Tetrahedron. 1992;48:9237-9250.
5. c) Le Gallic Y, Thesis, Rouen, 1992.
6. [3] Yus M, Chem.Soc.Rew. 1996; 152-161 and references therein.
7. [4] Yus M, Ramon DJ, J. Chem. Soc. Chem. Commun, 1991;398-401.
8. [5] 5 was obtained with 37% yield when the dehydrochloration was performed in tert-butanol: Magnani A, Mc Elvain SM, J. Chem. Soc. 1938; 60:2210-2213.
9. 2O: 93/7 elution.
10. [7] Ferreira H, Diplôme d'Etudes Approfondies, Rouen, 1995.
11. [8] 6 was obtained by cracking at 120°C of the corresponding chloroacetal, which is an industrial intermediate (Rhône Poulenc Co).
12. a) Ancel JE, Thesis, Rouen, 1992;
13. b) Duhamel L, Duhamel P, Ancel JE; Tetrahedron Lett, 1994;35:1209-1210.
14. 6:1E,3E (45%); 1.67 (s, 3H); 3.05 (s, 3H); 5.27 (d, 1H, J=12.8); 5.65 (s, 1H); 6.36 (d, 1H, J=12.8); 1E,3Z (55%): 1.40 (s, 3H); 3.12 (s, 3H); 5.42 (s, 1H); 6.17 (d, 1H, J=13.0); 6.55 (d, 1H, J=13.0).
15. 1H NMR (60 / 40), all trans is predominant. Four isomers were detected by HPLC: all trans, 13-cis, 9-cis and 9-cis, 13-cis.